Start on the Jamaican north shore, where powdery white sands run their way along the coast from the ivory stretches of iconic Seven Mile Beach, past the sheer-cut Negril Cliffs, through the luxury uber-resorts of Montego Bay, around the gushing Dunn’s River Falls, and out to where famous James Bond Beach gives way to the jungles of Ocho Rios in plumes of swaying coconut palms, juniper bushes, mangrove and tamarind.
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From the swaying palms and rugged cliffs of Los Haitises in the east to the old mineshafts and dusty trailheads of the Sierra de Bahoruco in the west, the surfing hotspots of Cabarete and Puerto Plata in the north to the urban sprawl of Santa Domingo and its concomitant colonial treasures in the south, the Dominican Republic has plenty of tricks up its sleeve! For most, the piece de resistance is Punta Cana, where strips of white sand run along the windward coast like glistening ribbons in the moonlight, punctuated only by the occasional luxury resort, its infinity pools butting up right to rollers of the Atlantic.
Flight Boston - London (BOS - LHR) $303+ Flight New York - London (JFK - LGW) $334+ Flight New York - London (JFK - LHR) $336+ Flight Newark - London (EWR - LHR) $340+ Flight Dallas - London (DFW - LHR) $358+ Flight New York - London (LGA - LHR) $372+ Flight Chicago - London (ORD - LGW) $374+ Flight Newark - London (EWR - LCY) $386+ Flight Chicago - London (ORD - LHR) $387+ Flight New York - London (JFK - LCY) $390+ Flight Newark - London (EWR - LGW) $399+ Flight Washington - London (IAD - LHR) $410+ Flight San Francisco - London (SFO - LHR) $417+ Flight Los Angeles - London (LAX - LHR) $422+
But Indonesia has more than just Bali. The nearby Gili Islands are another incredible island getaway. Both destinations make for a more active tropical vacation and the weather remains pretty constant all year round (though April to October sees slightly drier weather). Both Bali and the Gili Islands are close enough that you should be able to visit them both on your trip to really get the most out of this idyllic corner of the world.
Flight Atlantic City - Fort Lauderdale (ACY - FLL) $89+ Flight Atlanta - Fort Lauderdale (ATL - FLL) $105+ Flight Denver - Fort Lauderdale (DEN - FLL) $107+ Flight Houston - Fort Lauderdale (HOU - FLL) $111+ Flight Houston - Fort Lauderdale (IAH - FLL) $111+ Flight Philadelphia - Fort Lauderdale (PHL - FLL) $111+ Flight Washington - Fort Lauderdale (BWI - FLL) $113+
The largest of the Bahama islands, Andros is also the least populated, offering the chance to own a piece of your own island without the high price tag.  Here, locals make waterproof straw baskets, batik and other crafts, and visitors will also find mesmerizing blue holes, excellent bonefishing and diving. The island is home to the world’s oldest dive shop, the second largest coral reef in the Western hemisphere, and is covered with vast areas of wetlands that create channels perfect for bonefishing. Many visitors come to experience this “Bonefishing Capital of the World,” by staying at Bair’s Lodge, a plantation-style lodge situated between Deep and Middle Creek on the south end of the island offering a beachfront paradise with a picture-perfect white sand beach, swaying palms, fire pit and access to a flats skiff. The tidal paths found on this part of Andros provides water pathways to access the famous west side while offering protection from the winds, and creating a fertile, bait-rich environment that bonefish prefer. 

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These little coral islands are surrounded by excellent diving, snorkeling, and white sand beaches, and are filled with friendly locals. Private resorts litter the islands, and a vacation here is also very pricey. Luckily, Bangkok Airways offers cheap flights to and from Thailand. The best time to go to the Maldives is from November to May, when the weather is cool and dry. June through October sees wetter and hotter weather due to the monsoon season.
Start on the Jamaican north shore, where powdery white sands run their way along the coast from the ivory stretches of iconic Seven Mile Beach, past the sheer-cut Negril Cliffs, through the luxury uber-resorts of Montego Bay, around the gushing Dunn’s River Falls, and out to where famous James Bond Beach gives way to the jungles of Ocho Rios in plumes of swaying coconut palms, juniper bushes, mangrove and tamarind.
Glad to see you mentioned the Cook Islands – my husband and I went to Rarotonga for a week in 2008 and fell in love with it – can’t wait to someday bring our kids back there – they would love it, too! Very few people have actually heard of the Cooks, or know where they are, and while I like the “secrecy” of it, I wish more people would visit! Currently there are only 1-2 flights/week from the US – makes planning trips there a bit tougher!We only took a day trip to Aitutaki because of time, but it was probably the most beautiful place I’ve ever been. Glad to see you agree!
While technically a subtropical island, the Azores make for a great getaway if you’re looking for something beyond the standard resort getaway. The islands boast tons of hiking and beautiful nature. Rent a car and explore the winding roads of the main island, São Miguel Island, taking it secluded beaches and picturesque waterfalls. Best of all, it’s close to both Europe and North America and makes for a great stopover point if you’re traveling between the two.
Flight Denver - Chicago (DEN - ORD) $79+ Flight Houston - Chicago (HOU - ORD) $91+ Flight Houston - Chicago (IAH - ORD) $91+ Flight Boston - Chicago (BOS - ORD) $97+ Flight Dallas - Chicago (DFW - ORD) $97+ Flight Minneapolis - Chicago (MSP - ORD) $97+ Flight New York - Chicago (LGA - ORD) $97+ Flight Washington - Chicago (BWI - ORD) $101+ Flight Atlanta - Chicago (ATL - ORD) $108+
Glad to see you mentioned the Cook Islands – my husband and I went to Rarotonga for a week in 2008 and fell in love with it – can’t wait to someday bring our kids back there – they would love it, too! Very few people have actually heard of the Cooks, or know where they are, and while I like the “secrecy” of it, I wish more people would visit! Currently there are only 1-2 flights/week from the US – makes planning trips there a bit tougher!We only took a day trip to Aitutaki because of time, but it was probably the most beautiful place I’ve ever been. Glad to see you agree!
Glad to see you mentioned the Cook Islands – my husband and I went to Rarotonga for a week in 2008 and fell in love with it – can’t wait to someday bring our kids back there – they would love it, too! Very few people have actually heard of the Cooks, or know where they are, and while I like the “secrecy” of it, I wish more people would visit! Currently there are only 1-2 flights/week from the US – makes planning trips there a bit tougher!We only took a day trip to Aitutaki because of time, but it was probably the most beautiful place I’ve ever been. Glad to see you agree!
Great list Matt! Indeed, there obviously there are some spots on this globe I have to visit. Can confirm the Maldives though. Has changed over time, but then again, the first time they were still “exploring” their “tourist economy” potential. Been there twice now and although definitely more crowded still holds its appeal. Be prepared for culture shock though. If you return to the “civilised world” you will wonder about the rest of the grubby world and catch yourself day dreaming regularly. 😉

While technically a subtropical island, the Azores make for a great getaway if you’re looking for something beyond the standard resort getaway. The islands boast tons of hiking and beautiful nature. Rent a car and explore the winding roads of the main island, São Miguel Island, taking it secluded beaches and picturesque waterfalls. Best of all, it’s close to both Europe and North America and makes for a great stopover point if you’re traveling between the two.


Located in southern Thailand, this semi-off-the-map island is one of my favorites and the month I spent here remains one of my most fond memories. Here on Ko Lipe, the super-friendly locals bring in the daily catch for amazing seafood, as the island’s water is teeming with life. Accommodation is still basic, and most places turn off the electricity around midnight.
Flight Boston - London (BOS - LHR) $303+ Flight New York - London (JFK - LGW) $334+ Flight New York - London (JFK - LHR) $336+ Flight Newark - London (EWR - LHR) $340+ Flight Dallas - London (DFW - LHR) $358+ Flight New York - London (LGA - LHR) $372+ Flight Chicago - London (ORD - LGW) $374+ Flight Newark - London (EWR - LCY) $386+ Flight Chicago - London (ORD - LHR) $387+ Flight New York - London (JFK - LCY) $390+ Flight Newark - London (EWR - LGW) $399+ Flight Washington - London (IAD - LHR) $410+ Flight San Francisco - London (SFO - LHR) $417+ Flight Los Angeles - London (LAX - LHR) $422+

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This long and slender island is the most historic of the Out Islands, with the first English settlers arriving back in 1648.  Much of the architecture and way of life was influenced by these British Loyalists. Here you will find some of the island’s luxury resorts, massive coral reefs that create breathtaking backdrops, and miles and miles of beautiful beach that can often be enjoyed all to yourself, with many stretches of sand relatively deserted thanks to their secluded locales. Although Eleuthera is the fourth most populated island in The Bahamas, home to about 11,000, most who live here either fish for bounty or farm the rolling acres of pineapple plantations. The bakeries lure visitors in with their mouth-watering pineapple tarts from the island’s signature crop – Henry Sands homemade bread even won him an invitation to Princess Di’s wedding.
You know those pictures you always see of tropical bungalows in the water? That’s Tahiti. The name has long been synonymous with tropical paradise. One of the biggest honeymoon destinations in the world, Tahiti offers pure paradise and a lot of romance. Here you can relax in the sun, scuba dive, enjoy fine seafood, and take a morning dip right from your bungalow.
The largest of the Bahama islands, Andros is also the least populated, offering the chance to own a piece of your own island without the high price tag.  Here, locals make waterproof straw baskets, batik and other crafts, and visitors will also find mesmerizing blue holes, excellent bonefishing and diving. The island is home to the world’s oldest dive shop, the second largest coral reef in the Western hemisphere, and is covered with vast areas of wetlands that create channels perfect for bonefishing. Many visitors come to experience this “Bonefishing Capital of the World,” by staying at Bair’s Lodge, a plantation-style lodge situated between Deep and Middle Creek on the south end of the island offering a beachfront paradise with a picture-perfect white sand beach, swaying palms, fire pit and access to a flats skiff. The tidal paths found on this part of Andros provides water pathways to access the famous west side while offering protection from the winds, and creating a fertile, bait-rich environment that bonefish prefer.

It’s rare to have a sizeable international airport just minutes from the main attractions of a place, but Las Vegas has always been a place to break the rules. Its airport handles flights from all over the world, and it’s just 2 miles from the Strip. Free shuttle services and an onslaught of taxis await to whisk you to your hotel. Minutes later, when you’re out exploring, there are numerous ways to get around. It can often be quicker to walk between casinos especially when the traffic’s gridlocked, but taxis and buses ply the Strip and surrounding areas too.
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